Manufacture of tertiobutyl hydroperoxyde from renewable materials, tertiobutyl hydroperoxide thus obtained, and uses thereof

Abstract

The present application relates to a method for manufacturing tert-butyl hydroperoxide that includes the following steps: a) fermenting renewable raw materials and optionally purifying the same to produce a mixture containing at least butanol; b) dehydrating the butanol into butane; c) converting the butane into isobutene and optionally hydrating the isobutene to produce tert-butanol; d) reacting the product of step c) with hydrogen peroxide so as to produce tert-butyl hydroperoxide; and e) isolating the tert-butyl hydroperoxide. The invention also relates to tert-butyl hydroperoxide containing carbon atoms from renewable resources, to the compositions containing said tert-butyl hydroperoxide, and also relates to the use thereof as a polymerization initiator.

The invention claimed is: 
     
       1. A process for producing tert-butyl hydroperoxide from a renewable starting material comprising at least the following steps of:
 a) fermenting a renewable starting material and, optionally, purifying so as to produce a mixture comprising at least butanol; 
 b) dehydrating the butanol to form butene in the presence of a strong acid at a temperature of about 120° C.; 
 c) converting the butene to produce isobutene, and optionally hydrating the isobutene to produce tert-butanol; 
 d) reacting the product of step c) with hydrogen peroxide so as to produce tert-butyl hydroperoxide; and 
 e) isolating the tert-butyl hydroperoxide. 
 
     
     
       2. The process for producing tert-butyl hydroperoxide of  claim 1 , wherein step c) comprises hydrating the isobutene to produce tert-butanol, and step d) includes reacting the tert-butanol with the hydrogen peroxide. 
     
     
       3. The process for producing tert-butyl hydroperoxide of  claim 2 , wherein the step of hydrating the isobutene to give tert-butanol of step c) is carried out in the presence of dilute sulfuric acid, or in the presence of acidic ion exchange resins. 
     
     
       4. The process for producing tert-butyl hydroperoxide of  claim 1 , wherein the renewable starting material is a plant material selected from sugar cane, sugar beet, maple, date palm, sugar palm, sorghum, American agave, corn, wheat, barley, sorghum, rye, soft wheat, rice, potato, cassava, sweet potato, straw, wood, paper and algae. 
     
     
       5. The process for producing tert-butyl hydroperoxide of  claim 1 , wherein the fermentation step a) is carried out in the presence of  Clostridium acetobutylicum  or a mutant thereof. 
     
     
       6. The process for producing tert-butyl hydroperoxide of  claim 1 , wherein the fermentation step a) is followed by a step for isolating the butanol. 
     
     
       7. The process for producing tert-butyl hydroperoxide of  claim 1 , wherein the step c) comprises bringing the butene into contact with a tectometallosilicate which has a ferrierite crystalline structure, at a temperature of between 150° C. and 450° C., at a butene partial pressure of 0.5 bar and a total pressure of between 0.5 and 25 bar. 
     
     
       8. The process for producing tert-butyl hydroperoxide of  claim 1 , wherein the step d) is carried out in the liquid phase, in the presence of sulfuric acid, with continuous and vigorous stirring, at a reaction temperature of between 30° C. and 75° C. at atmospheric pressure. 
     
     
       9. The process for producing tert-butyl hydroperoxide of  claim 1 , wherein said strong acid of step b) is sulfuric acid (H 2 SO 4 ) or phosphoric acid.